Compounds with an acceptor and a donor group

Abstract

The present invention describes compounds having an acceptor group and a donor group, especially for use in electronic devices. The invention further relates to a process for preparing the compounds of the invention and to electronic devices comprising these.

Claims

1. A compound comprising at least one structure of the formula (I): ##STR00405## where the symbols used are as follows: Q is an acceptor that is represented by the formula (QL),
Q.sup.1-L.sup.1-  Formula (QL) in which L.sup.1 represents an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals; Q.sup.1 is an electron-withdrawing group; HL is a donor group; Ar.sup.a, Ar.sup.b is the same or different and is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals; R.sup.a and R.sup.b represent an aryl or heteroaryl radical, where R.sup.a and R.sup.b are joined by a ring closure effected by a bond between R.sup.a and R.sup.b; R.sup.1 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR.sup.2).sub.2, CHO, C(═O)R.sup.2, CR.sup.2═C(R.sup.2).sub.2, CN, C(═O)OR.sup.2, C(═O)N(R.sup.2).sub.2, S.sub.1(R.sup.2).sub.3, N(R.sup.2).sub.2, NO.sub.2, P(═O)(R.sup.2).sub.2, OSO.sub.2R.sup.2, OR.sup.2, S(═O)R.sup.2, S(═O).sub.2R.sup.2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, NR.sup.2, P(═O)(R.sup.2), —C(═O)O—, —C(═O)NR.sup.2—, —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals; or a combination of these systems; at the same time, two or more R.sup.1 radicals together may form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR.sup.3).sub.2, CHO, C(═O)R.sup.3, CR.sup.3═C(R.sup.3).sub.2, CN, C(═O)OR.sup.3, C(═O)N(R.sup.3).sub.2, S.sub.1(R.sup.3).sub.3, N(R.sup.3).sub.2, NO.sub.2, P(═O)(R.sup.3).sub.2, OSO.sub.2R.sup.3, OR.sup.3, S(═O)R.sup.3, S(═O).sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.3C═CR.sup.3—, —C≡C—, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═Se, C═NR.sup.3, NR.sup.3, P(═O)(R.sup.3), —C(═O)O—, —C(═O)NR.sup.3—, —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems; at the same time, two or more R.sup.2 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; and R.sup.3 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, in which hydrogen atoms may also be replaced by F; at the same time, two or more R.sup.3 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system.

2. The compound according to claim 1, wherein the Ar.sup.a and/or Ar.sup.b group in formula (I) is different from a donor group as per symbol HL.

3. The compound according to claim 1, wherein the donor group HL comprises a group selected from the formulae (H-1) to (H-3) ##STR00406## where the dotted bond marks the attachment position and Ar.sup.2, Ar.sup.3, Ar.sup.4 are each independently an aryl group having 6 to 40 carbon atoms or a heteroaryl group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.1 radicals; P is 0, 1, 2, 3, 4, 5 or 6; Z is C(R.sup.1).sub.2, Si(R.sup.1).sub.2, C═O, N—Ar.sup.1, BR.sup.1, PR.sup.1, POR.sup.1, SO, SO.sub.2, Se, O or S; R.sup.1 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR.sup.2).sub.2, CHO, C(═O)R.sup.2, CR.sup.2═C(R.sup.2).sub.2, CN, C(═O)OR.sup.2, C(═O)N(R.sup.2).sub.2, Si(R.sup.2).sub.3, N(R.sup.2).sub.2, NO.sub.2, P(═O)(R.sup.2).sub.2, OSO.sub.2R.sup.2, OR.sup.2, S(═O)R.sup.2, S(═O).sub.2R.sup.2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, NR.sup.2, P(═O)(R.sup.2), —C(═O)O—, —C(═O)NR.sup.2—, —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals; or a combination of these systems; at the same time, two or more R.sup.1 radicals together may form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR.sup.3).sub.2, CHO, C(═O)R.sup.3, CR.sup.3═C(R).sub.2, CN, C(═O)OR.sup.3, C(═O)N(R.sup.3).sub.2, Si(R.sup.3).sub.3, N(R.sup.3).sub.2, NO.sub.2, P(═O)(R.sup.3).sub.2, OSO.sub.2R.sup.3, OR.sup.3, S(═O)R.sup.3, S(═O).sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.3C═CR.sup.3—, —C≡C—, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═Se, C═NR.sup.3, NR.sup.3, P(═O)(R.sup.3), —C(═O)O—, —C(═O)NR.sup.3—, —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems; at the same time, two or more R.sup.2 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R.sup.3 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, in which hydrogen atoms may also be replaced by F; at the same time, two or more R.sup.3 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; and Ar.sup.1 represents an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.1 radicals, an aryloxy group which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.1 radicals, or an aralkyl group which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.1 radicals, where it is optionally possible for two or more, R.sup.1 substituents to form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R.sup.3 radicals.

4. The compound according to claim 1, wherein the donor group HL comprises a group selected from the formulae (H-4) to (H-26) ##STR00407## ##STR00408## ##STR00409## ##STR00410## wherein Y.sup.1 represents O, S, C(R.sup.1).sub.2 or NAr.sup.1; the dotted bond marks the attachment position; e is 0, 1 or 2; j is 0, 1, 2 or 3; h is 0, 1, 2, 3 or 4; p is 0, 1, 2, 3, 4, 5 or 6; Ar.sup.1 represents an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.1 radicals, an aryloxy group which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.1 radicals, or an aralkyl group which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more RI radicals, where it is optionally possible for two or more, R.sup.1 substituents to form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system which may be substituted by one or more R.sup.3 radicals; Ar.sup.2 is an aryl group having 6 to 40 carbon atoms or a heteroaryl group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.1 radicals; R.sup.1 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR.sup.2).sub.2, CHO, C(═O)R.sup.2, CR.sup.2═C(R.sup.2).sub.2, CN, C(═O)OR.sup.2, C(═O)N(R.sup.2).sub.2, Si(R.sup.2).sub.3, N(R.sup.2).sub.2, NO.sub.2, P(═O)(R.sup.2).sub.2, OSO.sub.2R.sup.2, OR.sup.2, S(═O)R.sup.2, S(═O).sub.2R.sup.2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, NR.sup.2, P(═O)(R.sup.2), —C(═O)O—, —C(═O)NR.sup.2—, —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals; or a combination of these systems; at the same time, two or more R.sup.1 radicals together may form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR.sup.3).sub.2, CHO, C(═O)R.sup.3, CR.sup.3═C(R.sup.3).sub.2, CN, C(═O)OR.sup.3, C(═O)N(R.sup.3).sub.2, Si(R.sup.3).sub.3, N(R.sup.3).sub.2, NO.sub.2, P(═O)(R.sup.3).sub.2, OSO.sub.2R.sup.3, OR.sup.3, S(═O)R.sup.3, S(═O).sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.3C═CR.sup.3—, —C≡C—, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═Se, C═NR.sup.3, NR.sup.3, P(═O)(R.sup.3), —C(═O)O—, —C(═O)NR.sup.3—, —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems; at the same time, two or more R.sup.2 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; and R.sup.3 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, in which hydrogen atoms may also be replaced by F; at the same time, two or more R.sup.3 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system.

5. The compound according to claim 3, wherein the Ar.sup.2 group is a connecting structure of the formula (LAr-1) ##STR00411## where X is the same or different at each instance and is N or CR.sup.1, or C if a group binds to X; the dotted bond marks the attachment position; s is 0, 1, 2, 3, 4, 5 or 6; R.sup.1 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR.sup.2).sub.2, CHO, C(═O)R.sup.2, CR.sup.2═C(R.sup.2).sub.2, CN, C(═O)OR.sup.2, C(═O)N(R.sup.2).sub.2, S.sub.1(R.sup.2).sub.3, N(R.sup.2).sub.2, NO.sub.2, P(═O)(R.sup.2).sub.2, OSO.sub.2R.sup.2, OR.sup.2, S(═O)R.sup.2, S(═O).sub.2R.sup.2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, NR.sup.2, P(═O)(R.sup.2), —C(═O)O—, —C(═O)NR.sup.2—, —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals; or a combination of these systems; at the same time, two or more R.sup.1 radicals together may form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR.sup.3).sub.2, CHO, C(═O)R.sup.3, CR.sup.3═C(R.sup.3).sub.2, CN, C(═O)OR.sup.3, C(═O)N(R.sup.3).sub.2, Si(R.sup.3).sub.3, N(R.sup.3).sub.2, NO.sub.2, P(═O)(R.sup.3).sub.2, OSO.sub.2R.sup.3, OR.sup.3, S(═O)R.sup.3, S(═O).sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.3C═CR.sup.3—, —C≡C—, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═Se, C═NR.sup.3, NR.sup.3, P(═O)(R.sup.3), —C(═O)O—, —C(═O)NR.sup.3—, —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems; at the same time, two or more R.sup.2 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; and R.sup.3 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, in which hydrogen atoms may also be replaced by F; at the same time, two or more R.sup.3 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system.

6. The compound according to claim 3, wherein Ar.sup.2 group is a connecting structure of the formula (LAr-2) ##STR00412## where X is the same or different at each instance and is N or CR.sup.1, or C if a group binds to X; the dotted bond marks the attachment position and t is 0, 1, 2, 3, 4, 5 or 6; R.sup.1 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR.sup.2).sub.2, CHO, C(═O)R.sup.2, CR.sup.2═C(R.sup.2).sub.2, CN, C(═O)OR.sup.2, C(═O)N(R.sup.2).sub.2, Si(R.sup.2).sub.3, N(R.sup.2).sub.2, NO.sub.2, P(═O)(R.sup.2).sub.2, OSO.sub.2R.sup.2, OR.sup.2, S(═O)R.sup.2, S(═O).sub.2R.sup.2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, NR.sup.2, P(═O)(R.sup.2), —C(═O)O—, —C(═O)NR.sup.2—, —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals; or a combination of these systems; at the same time, two or more R.sup.1 radicals together may form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR.sup.3).sub.2, CHO, C(═O)R.sup.3, CR.sup.3═C(R.sup.3).sub.2, CN, C(═O)OR.sup.3, C(═O)N(R.sup.3).sub.2, Si(R.sup.3).sub.3, N(R.sup.3).sub.2, NO.sub.2, P(═O)(R.sup.3).sub.2, OSO.sub.2R.sup.3, OR.sup.3, S(═O)R.sup.3, S(═O).sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.3C═CR.sup.3—, —C≡C—, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═Se, C═NR.sup.3, NR.sup.3, P(═O)(R.sup.3), —C(═O)O—, —C(═O)NR.sup.3—, —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems; at the same time, two or more R.sup.2 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; and R.sup.3 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, in which hydrogen atoms may also be replaced by F; at the same time, two or more R.sup.3 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system.

7. The compound according to claim 3, wherein the group is selected from structures of the formulae (Q-1), (Q-2), (Q-3), (Q-4), (Q-5), (Q-6), (Q-7), (Q-8), (Q-9) and/or (Q-10) ##STR00413## where the dotted bond marks the attachment position; Q′ is the same or different at each instance and represents CR.sup.1 or N; Q″ represents NR′, O or S; where at least one Q′ is N and/or at least one Q″ is NW; R.sup.1 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR.sup.2).sub.2, CHO, C(═O)R.sup.2, CR.sup.2═C(R.sup.2).sub.2, CN, C(═O)OR.sup.2, C(═O)N(R.sup.2).sub.2, Si(R.sup.2).sub.3, N(R.sup.2).sub.2, NO.sub.2, P(═O)(R.sup.2).sub.2, OSO.sub.2R.sup.2, OR.sup.2, S(═O)R.sup.2, S(═O).sub.2R.sup.2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, NR.sup.2, P(═O)(R.sup.2), —C(═O)O—, —C(═O)NR.sup.2—, —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals; or a combination of these systems; at the same time, two or more R.sup.1 radicals together may form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR.sup.3).sub.2, CHO, C(═O)R.sup.3, CR.sup.3═C(R.sup.3).sub.2, CN, C(═O)OR.sup.3, C(═O)N(R.sup.3).sub.2, Si(R.sup.3).sub.3, N(R.sup.3).sub.2, NO.sub.2, P(═O)(R.sup.3).sub.2, OSO.sub.2R.sup.3, OR.sup.3, S(═O)R.sup.3, S(═O).sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.3C═CR.sup.3—, —C≡C—, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═Se, C═NR.sup.3, NR.sup.3, P(═O)(R.sup.3), —C(═O)O—, —C(═O)NR.sup.3—, —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems; at the same time, two or more R.sup.2 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; and R.sup.3 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, in which hydrogen atoms may also be replaced by F; at the same time, two or more R.sup.3 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system.

8. The compound according to claim 3, wherein the Q.sup.1 group is selected from structures of the formulae (Q-11), (Q-12), (Q-13), (Q-14) and/or (Q-15) ##STR00414## wherein R.sup.1 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR.sup.2).sub.2, CHO, C(═O)R.sup.2, CR.sup.2═C(R.sup.2).sub.2, CN, C(═O)OR.sup.2, C(═O)N(R.sup.2).sub.2, Si(R.sup.2).sub.3, N(R.sup.2).sub.2, NO.sub.2, P(═O)(R.sup.2).sub.2, OSO.sub.2R.sup.2, OR.sup.2, S(═O)R.sup.2, S(═O).sub.2R.sup.2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, NR.sup.2, P(═O)(R.sup.2), —C(═O)O—, —C(═O)NR.sup.2—, —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals; or a combination of these systems; at the same time, two or more R.sup.1 radicals together may form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR.sup.3).sub.2, CHO, C(═O)R.sup.3, CR.sup.3═C(R.sup.3).sub.2, CN, C(═O)OR.sup.3, C(═O)N(R.sup.3).sub.2, Si(R.sup.3).sub.3, N(R.sup.3).sub.2, NO.sub.2, P(═O)(R.sup.3).sub.2, OSO.sub.2R.sup.3, OR.sup.3, S(═O)R.sup.3, S(═O).sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.3C═CR.sup.3—, —C≡C—, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═Se, C═NR.sup.3, NR.sup.3, P(═O)(R.sup.3), —C(═O)O—, —C(═O)NR.sup.3—, —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems; at the same time, two or more R.sup.2 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R.sup.3 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, in which hydrogen atoms may also be replaced by F; at the same time, two or more R.sup.3 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; X is N or CR.sup.1 and the dotted bond marks the attachment position.

9. The compound according to claim 3, wherein the Q.sup.1 group is selected from structures of the formulae (Q-16), (Q-17), (Q-28), (Q-29) and/or (Q-30) ##STR00415## wherein X is N or CR.sup.1; R.sup.1 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR.sup.2).sub.2, CHO, C(═O)R.sup.2, CR.sup.2═C(R.sup.2).sub.2, CN, C(═O)OR.sup.2, C(═O)N(R.sup.2).sub.2, Si(R.sup.2).sub.3, N(R.sup.2).sub.2, NO.sub.2, P(═O)(R.sup.2).sub.2, OSO.sub.2R.sup.2, OR.sup.2, S(═O)R.sup.2, S(═O).sub.2R.sup.2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, NR.sup.2, P(═O)(R.sup.2), —C(═O)O—, —C(═O)NR.sup.2—, —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals; or a combination of these systems; at the same time, two or more R.sup.1 radicals together may form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR.sup.3).sub.2, CHO, C(═O)R.sup.3, CR.sup.3═C(R.sup.3).sub.2, CN, C(═O)OR.sup.3, C(═O)N(R.sup.3).sub.2, Si(R.sup.3).sub.3, N(R.sup.3).sub.2, NO.sub.2, P(═O)(R.sup.3).sub.2, OSO.sub.2R.sup.3, OR.sup.3, S(═O)R.sup.3, S(═O).sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.3C═CR.sup.3—, —C≡C—, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═Se, C═NR.sup.3, NR.sup.3, P(═O)(R.sup.3), —C(═O)O—, —C(═O)NR.sup.3—, —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems; at the same time, two or more R.sup.2 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R.sup.3 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, in which hydrogen atoms may also be replaced by F; at the same time, two or more R.sup.3 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; the dotted bond marks the attachment position, and Ar.sup.1 represents an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.1 radicals, an aryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.1 radicals, or an aralkyl group which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.1 radicals, where it is optionally possible for two or more.

10. The compound according to claim 3, wherein the electron-withdrawing Q.sup.1 group is an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and has one or more electron-withdrawing substituents.

11. The compound according to claim 10, wherein the electron-withdrawing substituent is selected from F, fluorinated alkyl groups, CF.sub.3, C.sub.nF.sub.2n+1, C(═O)OR.sup.1, C(═O)N(R.sup.1).sub.2, NO.sub.2, CHO, C(═O)R.sup.1, S(═O)R.sup.1, S(═O).sub.2R.sup.1 and/or CN; R.sup.1 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR.sup.2).sub.2, CHO, C(═O)R.sup.2, CR.sup.2═C(R.sup.2).sub.2, CN, C(═O)OR.sup.2, C(═O)N(R.sup.2).sub.2, Si(R.sup.2).sub.3, N(R.sup.2).sub.2, NO.sub.2, P(═O)(R.sup.2).sub.2, OSO.sub.2R.sup.2, OR.sup.2, S(═O)R.sup.2, S(═O).sub.2R.sup.2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.2 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.2C═CR.sup.2—, —C≡C—, Si(R.sup.2).sub.2, Ge(R.sup.2).sub.2, Sn(R.sup.2).sub.2, C═O, C═S, C═Se, C═NR.sup.2, NR.sup.2, P(═O)(R.sup.2), —C(═O)O—, —C(═O)NR.sup.2—, —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.2 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R.sup.2 radicals; or a combination of these systems; at the same time, two or more R.sup.1 radicals together may form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R.sup.2 is the same or different at each instance and is H, D, F, Cl, Br, I, B(OR.sup.3).sub.2, CHO, C(═O)R.sup.3, CR.sup.3═C(R.sup.3).sub.2, CN, C(═O)OR.sup.3, C(═O)N(R.sup.3).sub.2, Si(R.sup.3).sub.3, N(R.sup.3).sub.2, NO.sub.2, P(═O)(R.sup.3).sub.2, OSO.sub.2R.sup.3, OR.sup.3, S(═O)R.sup.3, S(═O).sub.2R.sup.3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which may be substituted by one or more R.sup.3 radicals, where one or more nonadjacent CH.sub.2 groups may be replaced by —R.sup.3C═CR.sup.3—, —C≡C—, Si(R.sup.3).sub.2, Ge(R.sup.3).sub.2, Sn(R.sup.3).sub.2, C═O, C═S, C═Se, C═NR.sup.3, NR.sup.3, P(═O)(R.sup.3), —C(═O)O—, —C(═O)NR.sup.3—, —O—, —S—, SO or SO.sub.2 and where one or more hydrogen atoms may be replaced by D, F, Cl, Br, I, CN or NO.sub.2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and may be substituted in each case by one or more R.sup.3 radicals, or an aryloxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or an aralkyl or heteroaralkyl group which has 5 to 60 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and may be substituted by one or more R.sup.3 radicals, or a combination of these systems; at the same time, two or more R.sup.2 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; R.sup.3 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 20 carbon atoms, in which hydrogen atoms may also be replaced by F; at the same time, two or more R.sup.3 substituents together may also form a mono- or polycyclic, aliphatic, heteroaliphatic, aromatic or heteroaromatic ring system; and n represents an integer in the range from 1 to 20.

12. The compound according to claim 5, wherein Ar.sup.2 group is a connecting structure of the formula (LAr-1) or (LAr-2) ##STR00416## where X is the same or different at each instance and is N or CR.sup.1, or C if a group binds to X; the dotted bond marks the attachment position and t is 0, 1, 2, 3, 4, 5 or 6; R.sup.1 is defined in claim 5, and the difference between the index s in formula (LAr-1) and the index tin formula (LAr-2) is not more than 2.

13. An oligomer, polymer or dendrimer containing one or more compounds according to claim 1, wherein, rather than a hydrogen atom or a substituent, there are one or more bonds of the compounds to the polymer, oligomer or dendrimer.

14. A composition comprising at least one compound according to claim 1 and at least one further compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, host materials, matrix materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocker materials and hole blocker materials.

15. A formulation comprising at least one compound according to claim 1 and at least one solvent.

16. A TADF material, host material, electron transport material or hole conductor material which comprises the compound according to claim 1.

17. A process for preparing a compound according to claim 1 which comprises joining a compound comprising at least one donor group to an acceptor group in a coupling reaction.

18. An electronic device comprising at least one compound according to claim 1, wherein the electronic device is selected from the group consisting of organic integrated circuits, organic field-effect transistors, organic thin-film transistors, organic solar cells, organic optical detectors, organic photoreceptors, organic field-quench devices, organic electroluminescent devices.

19. The electronic device as claimed in claim 18, wherein the device is an organic electroluminescent device selected from the group of the organic light-emitting transistors, organic light-emitting diodes, organic light-emitting electrochemical cells and organic laser diodes.

Description

EXAMPLES

(1) The syntheses which follow, unless stated otherwise, are conducted under a protective gas atmosphere in dried solvents. The metal complexes are additionally handled with exclusion of light or under yellow light. The solvents and reagents can be purchased, for example, from Sigma-ALDRICH or ABCR. The respective figures in square brackets or the numbers quoted for individual compounds relate to the CAS numbers of the compounds known from the literature.

(2) Synthesis of the Synthons

Example S1

(3) ##STR00229##

(4) Procedure analogous to A. Sagadevan, et al., Green Chemistry, 17(2), 1113-1119; 2015. To a well-stirred mixture of 16.7 g (100 mmol) of carbazole [86-74-8], 34.6 g (250 mmol) of potassium carbonate, 2.5 g (10 mmol) of copper(II) sulfate pentahydrate [7758-99-8], 3.6 g (20 mmol) of phenanthroline, 300 ml of toluene and 50 g of glass beads are added 33.8 g (130 mmol) of 1-bromo-4-(2-bromethynyl)benzene [934-94-1], and then the mixture is stirred at 80° C. for 16 h. After cooling, the mixture is filtered through a Celite bed, the latter is washed through and the filtrate is concentrated to dryness. The residue is purified by flash chromatography (CombiFlash Torrent from Axel Semrau). Yield: 23.2 g (67 mmol), 67%; purity: 95% by .sup.1H NMR.

Example S100

(5) ##STR00230##

(6) A mixture of 34.6 g (100 mmol) of S1, 38.5 g (100 mmol) of 2,3,4,5-tetraphenyl-2,4-cyclopentadien-1-one [479-33-4] and 130 ml of diphenyl ether is heated to 265° C. for 24 h. After cooling and removal of the diphenyl ether under reduced pressure, the residue is extracted by boiling with 300 ml of ethanol, and the solids are filtered off with suction, washed three times with 100 ml each time of EtOH and dried under reduced pressure. The residue is purified by flash chromatography (CombiFlash Torrent from Axel Semrau). Yield: 51.4 g (73 mmol), 73%; purity: 98% by .sup.1H NMR.

(7) In an analogous manner, it is possible to prepare the following compounds using S1, i.e. 1-bromo-4-[2-(4-chlorophenyl)ethynyl]benzene [832744-28-2], as dienophile:

(8) TABLE-US-00005 Ex. Diene Product Yield S101 54% S102 56% S103 52% S104 63% S105 0 43% S106 55% S107 53% S108 67% S109 60% S110 0 63% S111 68% S112 73% S113 69% S114 57% S115 0 53% S116 62% S117 43% S118 66% S119 60% 0 S120 67% S121 61% S122 63% 0 S123 48%

Example S200: Buchwald Coupling

(9) ##STR00285##

(10) A mixture of 54.6 g (100 mmol) of S104, 16.7 g (100 mmol) of carbazole [86-74-8], 41.5 g (300 mmol) of potassium carbonate, 50 g of glass beads, 700 ml of toluene, 405 mg (2 mmol) of tri-Cert-butylphosphine and 225 mg (1 mmol) of palladium acetate is heated under reflux with good stirring for 24 h. After cooling, the salts are filtered off with suction through a Celite bed in the form of a toluene slurry, the bed is washed through three times with 100 ml each time of warm toluene, and the filtrate is washed once with 500 ml of water and once with 300 ml of sodium chloride solution and dried over magnesium sulfate. The solids obtained after the desiccant has been filtered off and the solvent has been removed are chromatographed (silica gel, dichloromethane) and then recrystallized from dimethylacetamide (DMAC). Yield: 46.1 g (73 mmol), 73%; purity: 97% by .sup.1H NMR.

(11) In an analogous manner, it is possible to prepare the following compounds, using 120 mmol of sodium tert-butoxide rather than potassium carbonate for couplings with secondary amines

(12) TABLE-US-00006 Ex. Reactants Product Yield S201 S104 122-39-4 58% S202 S104 1421789-16-3 70% S203 S104 205-25-4 68% S204 S105 56525-79-2 67% S205 S106 1257220-47-5 0 72% S206 S107 1466521-76-5 49% S207 S108 1257247-94-1 59% S208 S108 1431284-23-9 55% S209 S108 1316311-27-9 60% S210 S109 1024598-06-8 38% S211 S110 1199350-22-5 70% S212 S111 1382955-10-3 64% S213 S111 1060735-14-9 60% S214 S112 1609088-05-2 00 59% S215 S113 244-76-8 01 68% S216 S114 88590-00-5 02 45% S217 S115 244-63-3 03 48% S218 S116 1365647-82-0 04 58% S219 S117 135-67-1 05 62% S220 S118 1799501-71-5 06 60% S221 S119 955959-89-4 07 49% 08 S222 S120 1346669-46-2 09 55% S223 S121 1364890-88-9 0 47% S224 S122 1807860-07-6 51% S225 S123 1372775-52-4 45%

Example S300: Borylation

(13) ##STR00319##

(14) To a mixture of 70.3 g (100 mmol) of S100, 26.7 g (105 mmol) of 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) [73183-34-3], 29.5 g (300 mmol) of anhydrous potassium acetate, 50 g of glass beads (diameter 3 mm) and 700 ml of dioxane are added 543 mg (1.3 mmol) of S-Phos [657408-07-6] and 225 mg (1 mmol) of palladium(II) acetate, and the mixture is heated to 90° C. with good stirring for 16 h. After cooling, the mixture is filtered through a Celite bed in the form of a dioxane slurry, the bed is washed through with 300 ml of dioxane, the filtrate is concentrated to dryness, the residue is taken up in 500 ml of toluene, and the solution is washed three times with 100 ml each time of water and once with 200 ml of saturated sodium chloride solution and then dried over magnesium sulfate. The foam obtained after the desiccant has been filtered off and the solvent has been removed is recrystallized from ethyl acetate/methanol. Yield: 65.2 g (87 mmol), 87%; purity: 95% by .sup.1H NMR.

(15) In an analogous manner, it is possible to prepare the following compounds:

(16) TABLE-US-00007 Ex. Reactant Product Yield S301 S101 0 89% S302 S102 90% S303 S103 85% S304 S201 86% S305 S202 83% S306 S203 90% S307 S204 86% S308 S205 87% S309 S206 73% S310 S207 0 79% S311 S208 80% S312 S209 85% S313 S210 85% S314 S211 87% S315 S212 86% S316 S213 88% S317 S214 79% S318 S215 81% S319 S216 90% S320 S217 0 80% S321 S218 88% S322 S219 74% S323 S220 82% S324 S221 76% S325 S222 69% S326 S223 S327 S224 0 67% S328 S225 71%

Example P1: Suzuki Coupling

(17) ##STR00356##

(18) To a well-stirred mixture of 75.0 g (100 mmol) of S300, 28.1 g (105 mmol) of 1-chloro-3,5-diphenyltriazine [3842-55-5], 63.7 g (300 mmol) of tripotassium phosphate, 500 ml of toluene, 300 ml of dioxane, 500 ml of water are added 1.2 g (3 mmol) of S-Phos [657408-07-6] and 498 mg (2 mmol) of palladium(II) acetate, and then the mixture is heated under reflux for 16 h. After cooling, the organic phase is removed and washed twice with 300 ml each time of water and once with 300 ml of saturated sodium chloride solution, and then dried over magnesium sulfate. The desiccant is filtered off through a Celite bed in the form of a toluene slurry, the bed is washed through with 300 ml of toluene, the filtrate is concentrated to dryness and the residue is crystallized twice from dimethylacetamide. Further purification is effected by repeated hot extraction with n-butyl acetate, followed by fractional sublimation (p about 10.sup.−5 mbar, T about 330° C.). Yield: 47.9 g (56 mmol), 56%; purity: 99.9% by .sup.1H NMR.

(19) In an analogous manner, it is possible to prepare the following compounds, with products of molar mass greater than 1200 g/mol typically being freed of residual solvents by heating under high vacuum:

(20) TABLE-US-00008 Ex. Reactant Product Yield P2 S101 1215596-23-6 54% P3 S102 1613163-88-4 49% P4 S303 2915-16-4 59% P5 S304 3842-55-5 0 57% P6 S305 2915-16-4 53% P7 S306 29874-83-7 55% P8 S307 1300115-09-6 51% P9 S308 6484-25-9 49% P10 S309 24547-45-3 38% P11 S310 23449-08-3 55% P12 S311 864377-31-1 58% P13 S312 1616231-57-2 54% P14 S313 1689576-03-1 0 50% P15 S314 55635-65-9 57% P16 S315 1931136-94-5 51% P17 S316 3842-55-5 53% P18 S317 3842-55-5 59% P19 S318 1439929-51-7 55% P20 S319 334-04-7 52% P21 S320 371-88-6 56% P22 S321 80587-76-4 49% P23 S322 37084-03-4 44% P24 S323 334-04-7 0 47% P25 S324 3842-55-5 30% P26 S325 3842-55-5 P27 S326 15679-03-5 32% P28 S327 3842-55-5 27% P29 S328 3842-55-5 0 29%

Example: Production of the OLEDs

(21) 1) Vacuum-Processed Devices:

(22) OLEDs of the invention and OLEDs according to the prior art are produced by a general method according to WO 2004/058911, which is adapted to the circumstances described here (variation in layer thickness, materials used).

(23) In the examples which follow, the results for various OLEDs are presented. Glass plaques with structured ITO (50 nm, indium tin oxide) form the substrates to which the OLEDs are applied. The OLEDs basically have the following layer structure: substrate/hole transport layer 1 (HTL1) consisting of HTM doped with 5% NDP-9 (commercially available from Novaled), 20 nm/hole transport layer 2 (HTL2)/optional electron blocker layer (EBL)/emission layer (EML)/optional hole blocker layer (HBL)/electron transport layer (ETL)/optional electron injection layer (EIL) and finally a cathode. The cathode is formed by an aluminium layer of thickness 100 nm.

(24) First of all, vacuum-processed OLEDs are described. For this purpose, all the materials are applied by thermal vapour deposition in a vacuum chamber. In this case, the emission layer always consists of at least one matrix material (host material) and an emitting dopant (emitter) which is added to the matrix material(s) in a particular proportion by volume by co-evaporation. Details given in such a form as M3:M2:Ir(L2) (55%:35%:10%) mean here that the material M3 is present in the layer in a proportion by volume of 55%, M2 in a proportion of 35% and Ir(L2) in a proportion of 10%. Analogously, the electron transport layer may also consist of a mixture of two materials. The exact structure of the OLEDs can be found in Table 1. The materials used for production of the OLEDs are shown in Table 4.

(25) The OLEDs are characterized in a standard manner. For this purpose, the electroluminescence spectra, the power efficiency (measured in cd/A) and the voltage (measured at 1000 cd/m.sup.2 in V) are determined from current-voltage-brightness characteristics (IUL characteristics). For selected experiments, the lifetime is determined. The lifetime is defined as the time after which the luminance has fallen from a particular starting luminance to a certain proportion. The figure LD50 means that the lifetime specified is the time at which the luminance has dropped to 50% of the starting luminance, i.e. from, for example, 1000 cd/m.sup.2 to 500 cd/m.sup.2. According to the emission colour, different starting brightnesses were selected. The values for the lifetime can be converted to a figure for other starting luminances with the aid of conversion formulae known to those skilled in the art. In this context, the lifetime for a starting luminance of 1000 cd/m.sup.2 is a standard figure.

(26) Use of Compounds of the Invention as Emitter Materials in Phosphorescent OLEDs

(27) One use of the compounds of the invention is as emitter materials (TADF) in the emission layer in OLEDs.

(28) They are also usable as matrix/host material for phosphorescent emitters. The compounds according to Table 4 are used as a comparison according to the prior art. The results for the OLEDs are collated in Table 2.

(29) TABLE-US-00009 TABLE 1 Structure of the OLEDs HTL2 EBL HBL thick- thick- EML thick- ETL Ex. ness ness thickness ness thickness Ref.-D1 HTM — M1:IrRef1 HBM1 ETM1:ETM2 40 nm (88%:12%) 10 nm (50%:50%) 35 nm 30 nm D1 HTM — P1:IrRef1 HBM1 ETM1:ETM2 40 nm (88%:12%) 10 nm (50%:50%) 35 nm 30 nm D2 HTM — P4:IrRef1 HBM1 ETM1:ETM2 40 nm (88%:12%) 10 nm (50%:50%) 35 nm 30 nm D3 HTM — P4:IrRef1 HBM1 ETM1:ETM2 40 nm (80%:20%) (50%:50%) 35 nm 30 nm D4 HTM — P4:M3:IrRef1 HBM1 ETM1:ETM2 40 nm (60%:30%:10%) 10 nm (50%:50%) 35 nm 30 nm D5 HTM — P18:M3 HBM1 ETM1:ETM2 40 nm (60%:40%) 10 nm (50%:50%) 40 nm 30 nm D6 HTM — P18:M3:SER1 HBM1 ETM1:ETM2 40 nm (60%:35%:5%) 10 nm (50%:50%) 40 nm 30 nm

(30) TABLE-US-00010 TABLE 2 Results for the vacuum-processed OLEDs Ex. EQE (%) Voltage (V) CIE x/y LD50 (h) 1000 cd/m.sup.2 1000 cd/m.sup.2 1000 cd/m.sup.2 1000 cd/m.sup.2 Ref.-D1 18.8 3.2 0.34/0.62 190000 D1 18.9 3.0 0.33/0.62 240000 D2 19.2 2.9 0.34/0.62 230000 D3 19.4 2.9 0.33/0.63 340000 D4 19.0 3.1 0.34/0.62 360000 500 cd/m.sup.2 500 cd/m.sup.2 500 ccd/m.sup.2 500 cd/m.sup.2 D5 12.3 3.4 0.26/0.54 20000 D6 15.7 3.5 0.51/0.47 90000
Solution-Processed Devices:
From Soluble Functional Materials of Low Molecular Weight

(31) The iridium complexes of the invention may also be processed from solution and lead therein to OLEDs which are much simpler in terms of process technology compared to the vacuum-processed OLEDs, but nevertheless have good properties. The production of such components is based on the production of polymeric light-emitting diodes (PLEDs), which has already been described many times in the literature (for example in WO 2004/037887). The structure is composed of substrate/ITO/hole injection layer (60 nm)/interlayer (20 nm)/emission layer (60 nm)/hole blocker layer (10 nm)/electron transport layer (40 nm)/cathode. For this purpose, substrates from Technoprint (soda-lime glass) are used, to which the ITO structure (indium tin oxide, a transparent conductive anode) is applied. The substrates are cleaned in a cleanroom with DI water and a detergent (Deconex 15 PF) and then activated by a UV/ozone plasma treatment. Thereafter, likewise in a cleanroom, a 20 nm hole injection layer is applied by spin-coating. The required spin rate depends on the degree of dilution and the specific spin-coater geometry. In order to remove residual water from the layer, the substrates are baked on a hotplate at 200° C. for 30 minutes. The interlayer used serves for hole transport; in this case, HL-X from Merck is used. The interlayer may alternatively also be replaced by one or more layers which merely have to fulfil the condition of not being leached off again by the subsequent processing step of EML deposition from solution. For production of the emission layer, the triplet emitters of the invention are dissolved together with the matrix materials in toluene or chlorobenzene. The typical solids content of such solutions is between 16 and 25 g/I when, as here, the layer thickness of 60 nm which is typical of a device is to be achieved by means of spin-coating. The solution-processed green type 1 devices contain an emission layer composed of P:M:IrRef2 (X %:Y %:Z %); the red type 2 devices contain an emission layer composed of P:M:IrRef2:IrRef3 (X %:Y %:Z %:5%); in other words, they contain two different Ir complexes. The emission layer is spun on in an inert gas atmosphere, argon in the present case, and baked at 160° C. for 10 min. Vapour-deposited above the latter are the hole blocker layer (10 nm ETM1) and the electron transport layer (40 nm ETM1 (50%)/ETM2 (50%)) (vapour deposition systems from Lesker or the like, typical vapour deposition pressure 5×10.sup.−6 mbar). Finally, a cathode of aluminium (100 nm) (high-purity metal from Aldrich) is applied by vapour deposition. In order to protect the device from air and air humidity, the device is finally encapsulated and then characterized. The OLED examples cited are yet to be optimized; Table 3 summarizes the data obtained.

(32) TABLE-US-00011 TABLE 3 Results with materials processed from solution EQE Voltage LD50 (%) (V) (h) 1000 1000 CIE 1000 Ex. P:M:IrRef cd/m.sup.2 cd/m.sup.2 x/y cd/m.sup.2 Red type 2 devices Sol-Ref-Red1 M4:M5:IrRef2 17.4 6.2 0.66/0.34 240000 30%:40%:25% Sol-RedD1 P11:M5:IrRef2 18.3 5.8 0.66/0.34 290000 70%:0%:25%  Sol-RedD2 P11:M5:IrRef2 18.6 5.9 0.66/0.34 320000 50%:20%:25% Sol-RedD3 P28:M5:IrRef2 18.8 6.1 0.66/0.34 370000 70%:0%:25%  Green type 1 devices Sol-Ref-Green1 M4:M5:IrRef2 20.1 5.3 0.33/0.62 200000 20%:60%:20% Sol-GreenD1 P10:M5:IrRef2 20.6 54 0.33/0.62 230000 80%:0%20%  Sol-GreenD2 P10:M5:IrRef2 20.9 5.3 0.33/0.62 220000 50%:30%:20% Sol-GreenD3 P11:M5:IrRef2 20.8 5.1 0.33/0.62 240000 60%:20%:20% Sol-GreenD4 P13:M5:IrRef2 20.5 5.2 0.33/0.62 240000 50%:30%:25% Sol-GreenD5 P14:M4:IrRef2 20.2 5.0 0.34/0.61 250000 45%:30%:25% Sol-GreenD6 P18:M3:IrRerf2 20.0 52 0.32/0.63 310000 50%:35%:15% Sol-GreenD7 P25:M5:IrRef2 19.9 5.1 0.33/0.62 260000 80%:0%:20%  Sol-GreenD8 P28:M5:IrRef2 20.3 5.0 0.32/0.62 240000 75%:0%:25% 

(33) TABLE-US-00012 TABLE 4 Structural formulae of the materials used 00 01 02 03 04